Early Life and Career
Pocklington was born in Regina, Saskatchewan, to Basil Pocklington, an insurance executive who had immigrated from England as a young man, and his wife, Eileen (Dempsey), and grew up in London, Ontario.
The greatest influence on young Pocklington was the legendary motivational speaker Earl Nightingale and his best-selling recording, The Strangest Secret. "It literally stated, 'You become what you think about,' " Pocklington told his biographers. He says he still has the record today.
One of his earliest business ventures was to find old cars on the farms around his maternal grandparents' home in Carberry, Manitoba, buy them for $25, then ship them to Ontario by train, where he sold them for upwards of $500. Because of the West's dry, cold climate, the cars, many of them 25 to 40 years old, were in better shape than comparable vehicles that had been driven on Ontario's salted roads.
By the time Pocklington was 25, he owned his first car dealership, Westown Ford in Tilbury, Ontario. At the time, he was the youngest Ford dealer in Canada. Within a few years he had sold the Tilbury dealership and bought another in nearby Chatham. By 1971, when Pocklington was only 29, he left Ontario and moved west, where he bought Shirley Ford in Edmonton, Alberta.
Within a few years, Pocklington was running the most successful Ford dealership in Canada. He also had the cash flow to buy Edmonton's fledgling team in the World Hockey Association.
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